Milan's most recent memories of Arsenal are not entirely fond either, as the Gunners ran out 5-1 aggregate winners in their 2017-18 Europa League last 16 and also dumped the Rossoneri out of the 2007-08 Champions League, although the Italians exacted their revenge four years later.

Milan are starting afresh again this summer following the departure of Sergio Conceição as manager, with a familiar face returning to lead the Rossoneri. Massimilano Allegri guided Milan to the Scudetto in 2011, and he was appointed as Conceição’s successor at the end of a disappointing 2024–25 campaign.